Connecting The Dots (All The Way To Silicon Valley)

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something - your gut, destiny, life, karma, whatever.”
-Steve Jobs

It seems “the long-term” is something that just happens… possibly destiny. It’s easy to mentally grasp the cause and effect patterns of the short-term, and due to this, we containerize our thoughts into “short-term” and “long-term”. You’ve probably written down goals before, or have been instructed to in school. “First, write down your long-term goals. Now think about what small steps will get you there.” Makes sense… if the world was that simple. But the world is a complex environment that constantly changes.

So saying “do A, then B, and you will achieve C” is a oversimplification. A and B are moving targets, and in reality, there are hundreds to millions of As and Bs. Choosing which path to follow is the hard part.

Every moment in life is a choice you have control over. At any second, you could get in your car and go on a road trip to Vegas. At any second, you could pick up a book and learn something new… possibly marine biology? If your goal was to land a job, wouldn’t it be funny if your interviewer studied marine biology or was also just in Vegas? That kind of stuff happens!

I think embracing the chaos around decisions and results is the only mentality that makes sense. If nothing you do is meaningless, do what you love. Want to go on a road trip? Do it. Want to drop out of school? Do it. Life is too short to dwell on the past or containerize your future.

I think my path to Silicon Valley displays how seemingly random events can align — how dots can connect. As someone who is a methodical planner, I can say that it wasn’t my planning that brought be out here. I just did what felt right when opportunities — things I couldn’t have planned for — came my way.

So here fit is, a “brief” timeline of events in my life that led me to become an internet entrepreneur.

The Foundation

It’s the 4th grade (yes, this is truly the foundation). Growing up, my family frequently took vacations to Ixtapa, Mexico. I met an artist there who was skilled at drawing cartoons, especially a show called Dragon Ball Z (DBZ). I decided to replicate him, and actually grew to become talented. I developed a reputation around school for being a good artist, so I decided to teach others how to draw. As I gained a crowd, I noticed another crowd forming across the room. I walked over to see what the fuss was about. I then met Devneel, who was also drawing DBZ characters by coincidence — instant friendship. We became competitive at everything, from math worksheets to drawing. I started to love math and I developed an interest in design through drawing competitions.

My newfound competitive nature eventually led me to video games while my curious nature led me to computers. How the heck did those things work anyways? And thus, the nerdy part of my life begins! In middle school, I joined video gamer teams known as “clans” and joined overclock.net, a computer enthusiast forum. I started building computers and gaming websites. I also started making desktop backgrounds in Photoshop for everyone on overclock.net. This lasted all the way into high school, and by senior year, I was rocking out designs, PHP, and awesome K/D ratios — that sure brought the ladies (not :P). I thought about monetizing my abilities, but was too entrenched in video games to care. I also wasn’t putting any effort into school. I never studied, not even for AP exams, but somehow managed to do well enough to get into UIUC for Computer Engineering. Lucky me… I was barely average at the time for admissions, had no extra-curriculars, and no backup schools interested me.

College Begins

Getting into the University of Illinois’ Computer Engineering curriculum was a big deal. At the time, it was ranked 3rd in the nation, right behind MIT and Stanford. I had to prove myself. After getting situated in my dorm, I immediately quit gaming and erased them off my computer. Devneel, who was also admitted to UIUC, and I met up within the first week of school and subsequently decided to build a startup together. We both had coding experience, I could design, and two others joined on as co-founders. Instarta was born, a text-message polling platform for politicians. They could blast questions to their constituents who would then vote to help decide the strategic direction of their city, state, and ultimately nation. I got the bug for entrepreneurship… big-time.

While this was starting, I was also commonly going to info sessions for student organizations on campus. My roommate was walking out the door to a information session that I hadn’t heard about… but I was tired. Then he said “free pizza,” and we walked over to the engineering campus. I was introduced to Engineering Council that day and was elected as their freshman committee’s webmaster a week later. I moved up in the organization throughout my sophomore and junior years, eventually became Vice President and developed numerous connections on campus. During the start of my Junior year, I met the student body president through random Engineering Council activities.. He invited me to a party, and although I barely knew him, I decided to go. At that party I met Jason, a friend of his. I had heard of Jason before, as he had won numerous business case competitions and was known as the kid who rejected Wharton. We talked business consulting, student organizations, and became friends quickly.

A Competition Network

Back to sophomore year: Instarta was going well. We had developed the technology to blast text-messages and receive messages en masse. When we went to demo the product, we had multiple connections lined up and beta politicians users. When we were ready for them to jump on, however, political season was in full gear and no one wanted to take the risk. We got screwed. Instarta discussed a buyout offer from a political party, but we didn’t even negotiate because we wanted to build a non-partisan platform. Another year chugged along as Instarta began pivoting through different products and technologies. I learned resilience.

As Instarta slid downhill, I was enrolled in a “High Tech Venture Marketing” class. I had coffee with my professor, who ran the school’s entrepreneurship center, and she told me about her problems managing a business plan competition. Schools across the nation had the same problem, and I knew a simple website could be a solution. Contendable, a website to manage and compete in competitions, was born. I was both a programmer and designer, but didn’t have time for both. After learning from Instarta, I also knew I wanted help on the business end of things. So who did I know that would be suitable? Who would know the market well? I met up with Jason, and he joined on as a co-founder. While the product designs were being fleshed out, we enrolled our company into the Cozad 2011 New Venture Competition. Ironically, we ended up winning. We won a competition that our internet application was designed to assist! We earned a cash prize, legal help, and incubator space in Chicago for summer 2011.

We decided we wanted more help on the development side, so we both used our personal connections. Jason had a friend named Will, who I had heard of before for being a top-notch computer science student. We met with Will over coffee and I showed him the designs for Contendable.com. He liked the product, but unfortunately had no time as he just quit Microsoft to work on another startup called Piazza. Coffee was over, and we moved on.

We found one programmer and pushed on product development while talking to some Venture Capitalists. We had an offer for some funding, but rejected it because it wasn’t very enticing and Jason was really excited about his consulting internship. Jason had received the internship offer I had really wanted (I wanted to test out the consulting lifestyle). I ended up getting a job I was happy with in downtown Chicago. At this point, we were seeing lackluster progress on development, so I said screw it, and started learning Ruby on Rails to build the product myself. I was already juggling twenty things, but this was my chance to make something great.

Summer 2011

After final exams, summer began. I had a cool, relaxing week off before work started… so naturally I put in 15 hours of work a day into Contendable. I packed all of my things and moved into an Art Institute dorm room in the middle of downtown Chicago. I had always wanted to live downtown, so this felt incredible. A day later I started by job as a business consultant. Everyone at work was accountable and upbeat. The offices were clean, neat, and modern, a huge upgrade from what I had experienced at GE the previous year. The other three interns were also pretty cool, and I quickly got comfortable in the environment. I was living with 80-100 people my age in the middle of downtown Chicago, I had just turned 21, and 10 of my friends were within walking distance. So badass.

On day 2, Tuesday, I’m grabbing a quick dinner with my parents when I get an email. It’s from Will.

Apparently Piazza, the company he joined, was about to close $2M dollar financing round with Sequoia Capital, arguably the biggest name in VC. Huge deal. Will simply says “We need a designer. Come over to Palo Alto for the summer.” If Palo Alto sounds familiar, it’s because that’s where Google, Facebook, and every huge tech company got their boost. It’s the worldwide heaven for entrepreneurs and computer geeks. I disregarded the email a little, thinking about how much I loved where I was at that time. This wasn’t the time to take a risk… I had it all going for me. The back of my mind was wandering, though. I loved entrepreneurship, even through the thick and thin. I knew what life would be like in Chicago as a consultant. I had never been to California before, let alone worked in Palo Alto. If I didn’t go now, I may never go…. shit shit shit.

I called many friends that night, and the advice I received shouldn’t have been surprising. They all said “It sounds like you really want to go.” My mind was already made up, I just didn’t realize it. I get a call from Piazza’s CEO, who sounded intelligent and confident. I figured the Valley was crawling with talented people. Since I wanted to learn from the best, I had to go. I left comfort and stability for a dream.

I arrived in Palo Alto and started working the day I got in. I picked up the code and design behind Piazza in a couple hours and pushed live changes the first day — it was awesome. I lived in Photoshop during the day and Textmate/Google Docs at night (coding Contendable’s backend in rails and getting business development/product feedback done). It was hard: I was only pulling 4-5 hours of sleep a night, but I was in the Valley. To make the situation harder, I couldn’t find housing. So I lived in the office for two weeks. That includes washing my hair in the office’s sink. Yeah, not exactly California Dreamin’.

Backplane

I started networking by getting coffee with random people in the valley, but little did I know that my next step was 20 feet away from my desk. Piazza shared office space with Backplane, a startup I knew nothing about. I just knew the two guys working in the office had a fog machine in their tiny 10’ by 10’ office and visualized tweets about Lady Gaga on the wall with a projector. I peeped my head in and asked “What the hell do you guys do?” The startup, Backplane, had the idea to create a platform for “fans” — and they were starting with Lady Gaga’s Littlemonsters.com. While working on Contendable at night, I started hanging out with a co-founder of Backplane. He helped me design Contendable and I helped him with Littlemonsters. As I learned more about Backplane, it became more intriguing. People form communities around lots of things, and Contendable was about community around competitions. What made me passionate for Contendable made me passionate for Backplane, but I thought nothing of it.

About 40 days into my internship at Piazza, I opened up my email and found an offer letter from Backplane. It ended with “Maybe it’s time to try something new.” But I still had a year of school left, what was I going to do…. drop out? Hah!

I dropped out and joined Backplane as the first hire. We’re now rocking it, empowering togetherness, and the dream is coming together. I’ll write a post about that later.

It’s hard to say what would have happened if any of these stepping stones were moved or removed. It’s hard to determine how any of this actually works.

If I didn’t ask Jason to be my partner, would I have ever met Will? If Instarta never failed and two years of solid work wasn’t thrown down the drain, would I have been able to leave the Midwest and migrate to the Valley?

I don’t know. All I know is this: I feel like I’m in the right place, right now. Thus, I won’t be giving 90% or 99%, I’m giving it my all. =)